


Messed-Up Kind of Love

by WinterWolf610



Category: Supernatural
Genre: Anal Sex, Bi Dean, Bisexual Dean, Bottom Dean, Dom Castiel, Dominant Castiel, Hand Jobs, Love Triangle, M/M, Oral Sex, Porn With Plot, Sex Toys, Sub Dean, Submissive Dean, Top Crowley, blowjob, dom Cas, dominant cas, moderate angst
Language: English
Status: Completed
Published: 2014-08-22
Updated: 2014-08-22
Packaged: 2018-02-10 16:30:13
Rating: Explicit
Warnings: No Archive Warnings Apply
Chapters: 1
Words: 4,099
Publisher: archiveofourown.org
Story URL: https://archiveofourown.org/works/2031948
Author URL: https://archiveofourown.org/users/WinterWolf610/pseuds/WinterWolf610
Summary: <blockquote class="userstuff">
              <p>Thinking that Castiel thinks of him only as a friend, Dean repeatedly falls into bed with Crowley. But when he realizes that Cas shares his feelings, Dean finds himself forced to choose between the Angel of The Lord and King of Hell.</p>
            </blockquote>





	Messed-Up Kind of Love

The situation was impossible. Dean Winchester knew he was fucked. Figuratively of course, but also at the moment, he was literally getting fucked.

The Demon King Crowley had him on all fours on a massive bed, legs all spread and ass in the air. With his hands on Dean's hips, Crowley pulls Dean back onto the demon's massive cock as he surges forward, resulting in the hunter being penetrated deeper than he even thought possible. The demon was tireless, setting a quick pace that Dean was sure would leave him bedridden tomorrow. 

The demon leans forward to growl dirty promises in his ear of how good he was going to get fucked tonight. But Dean heard none of it. He was imagining another supernatural being with a low, growling voice pounding into him. Blue eyes and messy hair. An Angel of The Lord who probably would never pound Dean into the mattress the way he wanted to be. 

And that was the problem. Dean was pining for his endearingly awkward angel even when he was furiously taking it up the ass for the charming and well-endowed King of Hell. But Cas had given him no indication that he wanted the same things Dean wanted. This had lead to Dean falling into bed with Crowley of all people. 

Dean still isn't quite sure how it happened but it started with him going to a bar and getting so drunk after seeing Cas that going home with the sympathetic demon sounded like a good idea. Dean woke up the next morning with a sore ass, the motel bathtub full of some kind of tropical fish and a couple of black chickens wandering around but he was still more relaxed than he's been in a while. 

It became routine to go out on dates with Crowley or have quiet nights in, cooking dinner and watching tv together. Crowley would listen patiently as he complained about Cas, and about his miserable life. Crowley would be there for Dean. Every meeting ended up like this, with Dean under the demon. Crowley could take it all away for a few hours and Dean needed it. Dean would never admit it, but he was happy with his arrangement with Crowley. 

Even still, he kept it secret. Crowley did too but for Dean's sake. Capable as he was, Crowley still didn't want any would-be contenders for the throne going after the hunter. In his dark, twisted demonic heart, Crowley cared what happened to Dean. Not that he would admit it either, but the older Winchester made him feel almost human again.

And nothing was more human than having sex for pleasure. Crowley certainly enjoyed it well enough. He had sold his soul for a little more oomph below the belt so he intended to make good use of it. He could still feel the tension in the body under his. With renewed purpose he begins to thrust into the hunter, striving hard to maximize the pleasure for both of them. He flips Dean around so he can stare into those dilated bright green eyes as they close, overcome with the moment. Dean can no longer hold back his moans as they fall off the edge together. 

Dean falls backwards onto the bed, boneless and utterly spent. He smiles fondly at Crowley as he cleans them both up and eases his human lover into bed. He knows Dean won't fall asleep until Crowley joins him but he takes his time, savoring this surprisingly tender moment between them. He joins Dean under the covers and was surprised to find that the hunter loves to cuddle after sex the first time, but he's grown quite fond of it himself. Dean's asleep as soon as he feels Crowley's arms wrap securely around him. 

As Crowley stares at his lover, he's amazed at how much younger he looks when he's fallen asleep after their vigorous joining. There are no frowns or lines on his face and his mouth is hanging open, quite adorably really, as he snores softly. Even after everything he's been through, the hunter is still fragile and a bit broken, largely because his little brother Sammy was out of the picture now. They don't talk specifically about that because it's too painful for Dean.

Crowley wants to prove to Dean that he deserves to be loved. They both do. Once they stopped trying to kill each other, Crowley grew even fonder of the elder Winchester. He vows then, silently to himself in that moment, that he will make Dean Winchester feel loved. 

The next morning, however, Dean woke up to a cold and empty bed. Mentally cursing Crowley for not being there to take care of his morning wood, Dean throws off the covers, rubs his eyes and stretches before realizing he's not alone as he thought. That blue-eyed, messy-haired Angel of The Lord Dean is so fond of is staring at Dean's bare and partially erect manhood. 

"Dammit Cas! We've talked about this!" This isn't the first time Dean's angel watched over him when he was sleeping. He wouldn't have minded so much if it didn't interfere with Crowley staying the night. Dean was used to it but hated to wake up alone. Crowley seemed to know that and stayed whenever he could. Castiel, however, was oblivious to this, and many other things about Dean. Dean really wishes he would take notice. 

"Apologies. I came to see how you were doing." Cas had averted his eyes by now. 

"And did you like what you saw?" Dean teased as he covered himself with the blankets, knowing his flirtation would go over the angel's head so he began to mentally prepare himself for taking a cold shower this morning. He had been hoping not to shower alone this morning. 

"I don't understand Dean. Did you wish for me to tell you that your genitals are of a pleasingly average size and-"

"Cas, buddy, stop right there. You're not supposed to look at other guys' junk when they're sleeping. Give me some time to wake up and shower Cas. Go watch some Dr. Sexy or something. I'm going to shower." 

Cas looked like he was going to argue but after seeing the look on Dean's face, he didn't. Dean was more awake now, and this made him more aware of how much his ass hurt. Dean wishes Cas wasn't there or he'd lay in bed all day, relishing the constant remind of what he'd done to get such a good fucking. Instead, he was going to have to make up an excuse for walking funny and avoid Cas's angelic healing mojo because that would definitely tell Cas that Dean had been lying to him. 

Looking around, he found the super soft pair of pajama bottoms Crowley had bought him on his bedside table. He certainly hadn't put them there so he mentally thanked the demon for it. He put them on and walked gingerly to the shower and got under the cold spray. The soreness was a welcome reminder that someone cared about him enough to know that he needed some physical affection. As much as he wanted Crowley to mark him, they both knew it would be too obvious a sign so they settled for Crowley making sure Dean felt it the next day.

Earlier in their relationship, if you could call it that, Crowley had healed everything and left no trace of their lovemaking. As soon as he realized Dean was unhappy with this, he adjusted. Anything Dean wanted, Crowley would give him. It was surprisingly caring for a man who ruled Hell with an iron fist. 

Dean honestly wondered what Crowley wanted from him. He knew he was good-looking and it probably flattered the demon's ego that one of the best hunters in the world would bend right over for him and beg to be stuffed full by his glorious cock. But Crowley never made Dean feel like he was just a hole to be filled. Crowley was honest about his desires and they sometimes got into some really kinky sex but he still treated Dean as if he were something precious.

It was all very strange. Dean wondered if the demon's obvious lust for him was a cover for something else. After all, maybe Crowley wanted something more and was worming his way into Dean's good graces before he made his move. Dean could only hope that if there was a price to pay, it wouldn't be too much to bear. After all, he'd lost too much already. 

As Dean finished his shower, he realized that he'd spent the whole time thinking about Crowley when Cas had been peeping on him right before. Crowley had shown Dean that he got off on a bit of voyeurism. He'd certainly taken care of himself to thoughts of Castiel watching him jerk off. This morning's occurrence should have had him touching himself in the shower but his thoughts were too focused on Crowley. 

The truth was that he never thought of Crowley so much as when he was with Castiel, and he never thought so much of Cas than when he was with Crowley. He was happy to indulge Crowley's lust for him but mostly because he was sure that Cas would never be more than platonically in love with him. Crowley was a good fuck and a pleasant enough date and Dean didn't want to come on to strongly with Cas for fear of losing having at least his friendship. Dean was fucked in every sense of the word.

Dean walked out to see Castiel indeed watching Dr. Sexy. Castiel looked up at him in surprise. With great concern and seriousness he informed Dean "Dr. Sexy seems to have sex appeal." 

"You know what sex appeal is?" Dean asked, honestly surprised. 

"Crowley told me once that I had it," Cas replied casually. 

"He what? When was this?" Dean sputtered. 

"When he proposed to me-"

"WHAT!?!"

"-that we go after Purgatory together," Cas finished. 

"Oh," Dean said sheepishly. He was getting sloppy, letting his jealousy over Cas show like that, even though though he was technically romantically involved with Crowley. Cas obviously didn't return his feelings so there was no point in acting on them.

"You are jealous of my former association with the King of Hell?" Cas questions, tilting his head to the side and squinting at Dean. 

"No I- I just... I, uh, care about you, Cas," Dean let slip. He was blushing deeper by the second and he wishes more than anything that Crowley was here. "Anyway, you want to go grab breakfast?"

"I shall watch over you, Dean." The angel looked at him so earnestly Dean mentally cursed himself. Now that Cas was a full angel again, food tasted like molecules to him. 

"Right... Baby's outside." Dean lead the way to his car, trying his damnedest to walk normally but it didn't fool the angel who had rebuilt his body after thirty years of Hell's tortures and another ten of committing them himself. 

"Dean, are you injured? Your gait is unsteady and you are more bowlegged than usual." 

Dean put on his most charming smile before turning back to the angel. "Just slept a little funny. Long night, you know," he winked at the angel before turning his back to Cas. This is why he didn't see Cas's hand coming forward to heal him. As soon as he felt the angel's touch, he knew his secret was out. 

Dean could barely look up at the angel. Big blue eyes stared forlornly back at him. "You're not jealous of me. You're jealous of Crowley." And with that he was gone. Dean sank to his knees and though he'd deny it later, he wept for being stupid and not seeing Cas's feelings for him and now losing his beloved angel, perhaps this time for good. Dean didn't know how to fix this so he did the only think he knew how to do in this situation: get really drunk and make bad decisions. 

He was very glad the next morning that the woman who he took home last night was nowhere to be found. To his surprise, he also didn't have a hangover. As he wandered out to the kitchen in the nude, he realized there was a full American breakfast laid out for him with a note tied to the rose in a vase on the center of the table. 

To his greater surprise, the note was from Crowley. It read:  
 _Squirrel,_  
 _Sorry little miss whatshername couldn't stay for breakfast with you. I, at least, can assure you that I do enjoy our little rendezvous. Heard what happened with your angel buddy. If you need a shoulder to cry on or a dick to ride on, you know how to reach me._  
 _Toodles,_  
 _~C_

Dean stared at it for a moment longer before digging into the breakfast the demon king had laid out for him. It was still warm and included all of his favorite things. Despite his uncertainty about the nature of his relationship with Crowley and what a dick he could be, he had to admit the demon was pretty incredible at anticipating his needs. 

What the hell, might as well call him up now. Couldn't exactly call up Cas. He could pray to him, but he probably wouldn't listen right now anyway. Maybe later though. Right now Crowley sounded far more promising a prospect. 

Dean made the arrangements to summon the King of Hell. He appeared immediately, eagerly awaiting the hunter's call. For once he didn't look smug. He looked concerned actually. Dean wasn't sure what to make of that.

"Thanks for breakfast, Crowley," Dean said by way of greeting. 

"Anything for my favorite hunter," he replied, not insincerely. He seemed to content to wait for Dean to make the first move, for which the hunter was very thankful. Dean launched himself at the demon, claiming his lips forcefully. Crowley indulged him, but when they broke apart, he just pulled the hunter into his lap on the couch and started rubbing him soothingly. 

Dean melted into the touch and let go of himself. He broke down and cried. Crowley thankfully said nothing about it and just held him, softly comforting him. Dean buried his head onto Crowley's shoulder, tears staining the demon's expensive suit but he didn't seem to mind.

When Dean had cried himself out, Crowley put him to bed and made him drink something. He did all of this without words, much to the hunter's surprise.

"Stay. Please," Dean asked simply and Crowley made no move to refuse. He simply got in bed with the hunter and pulled him right to his chest. Both of them drifted off before long. 

It was mid-afternoon by the time they Dean woke up again in a warm tangle of limbs. Dean decided he knew what he wanted in this moment. He dove under the covers to take Crowley's cock into his mouth.

"Dean... Oh!" gasped Crowley sleepily. "Hell of a way to wake up. Oh Jesus!" Dean was pleased that the demon couldn't stifle his moans as the hunter sucked his huge cock and bobbed his head as he took it down his throat. "God in Heaven!" The more Crowley took the Lord's name in vain, the better Dean knew he was doing. 

And Crowley was behaving himself, not bucking up to choke the hunter but instead letting Dean work at him. He did, however, throw the blankets aside to watch the hunter gobble him down hungrily. Crowley made no secret that he loved to see Dean on his dick, whether it be between his lips, down his throat, or up his ass. Watching Dean now was causing him to fist his hands in the sheets and lock their eyes together in the ecstasy of the moment as Dean sucked him to completion. 

Crowley reached down to tenderly cup Dean's jaw and bring Dean's mouth up to his for a sweet but dirty French kiss, letting his spent tender cock fall lazily from the hunter's full lips. Tasting himself in Dean's mouth stirred something dark and possessive in him and made him crave more. He wanted to take his hunter in hand and make him spill his pleasure, blissfully forgetting what had made him weep in the first place. 

He started to grip Dean gently but firmly at first. With him on all fours over the demon, Crowley found he couldn't get much leverage so he flipped them. A soft puff of air escaped Dean's lips as he hit the soft mattress. His eyes were wide with wonder as Crowley picked up the pace, reading the signals Dean's body was betraying. The feeling was so much more intense than Dean had ever felt. His lips were quivering in anticipation as he got closer and closer to the edge. 

When he finally released, it was as if a dam had burst. Dean forgot for that moment everything that was bad and wrong with his life and the world and simply existed, savoring the pure and simple sensations. The last thing he sees before he drifts off into the most peaceful sleep he's ever known is a bittersweet look on Crowley's face, which is far more human than Dean thought him capable of. 

When Dean awakes for the third time that day, it's nighttime and he isn't in the same room he fell asleep in. Panicked, he jolts up only to see big sad blue eyes staring at him. "Cas..." Dean begins, unsure where to begin considering that the angel had jealously left him after finding out he was sleeping with Crowley. "How did I get here?" he started, figuring that was as good an opening as any. 

"Crowley brought you here," stated the angel, his gaze never leaving Dean's. 

"Crowley? Why?" 

"He said you deserved to be loved. He seems to think me more capable of loving you than he is. I do not see how though. He is more powerful than I am and his penis is-"

"Whoa, whoa, whoa Cas, stop right there," interrupted Dean. "You don't need any of that to love someone. I'm, well, I'm sorry Cas. I- I didn't realize you liked me back... I ran to Crowley because I didn't think I'd get anywhere being in love with you. I had no idea. I'm not very good at reading interest in other guys. I knew Crowley would take me as I was. I liked how things were with him but I never stopped thinking about you. I've been in love with you for a long time and just never realized my own feelings until what I thought was too late. But maybe it's not too late." Dean looked up at Cas hopefully. 

"Dean I return your feelings but you are still involved with Crowley. I am not him. I am not willing to give you up or share you or whatever he meant by bringing you to me. You will have to choose between us Dean. I want all of you Dean. I want a relationship with you."

"Don't take this the wrong way but I need to talk to Crowley." He did, after all. He wasn't sure if he could give up Crowley and make things work with Cas. He was so sure he'd do something to screw things up in some unforgivable way and Cas would finally leave for good. Crowley had been forgiving of Dean's flaws and missteps, laughed them off and maybe gave Dean a playful spanking. Dean wasn't sure if Cas would be so indulgent. 

Cas didn't understand humans the way Crowley did. And Cas was so intense that it still put Dean on edge. He'd be scared to death to mess up anything with Cas any time they'd be together. But then again, Cas had already given so much for Dean. He repeatedly chose Dean over all of Heaven, his family. He went to extreme lengths to spare Dean any anguish that he could. Dean couldn't determine if that quality would be good or bad in a relationship. On the other hand, the demon didn't tell his minions about their liaisons to protect him but Crowley didn't spare a thought about using Dean as monster bait. He had no problem letting Dean handle his own if he wasn't truly in danger. He wasn't sure Cas would give him the same freedoms.

Dean couldn't decide. It was impossible. As he came back from his thoughts, he saw the same hopeless expression on Cas's solemn face. "I see how it is Dean. I wish you and Crowley well." He moved to leave but Dean reached out and gripped his shoulder tightly. 

"Cas, buddy, wait. I need you. Don't leave. Please," begged Dean. Dean Winchester didn't beg. But he did to Cas and he did to Crowley. 

"All of me?" inquired the angel, turning back and daring to let himself hope. 

Dean hesitates for a moment. Suddenly he can see Crowley sitting at a desk before him in a fancy office. "I've only got you for a moment but I just want to tell you that you deserve to be loved. Maybe right now you have a better shot of that with the angel. Go give this proper relationship thing with Castiel a try. You've both wanted it so much for so long. If it doesn't work out, you can always come back to me." 

Dean finds himself flung back to the moment he just left before he can even respond to Crowley's magnanimity. "All of me?" inquired the angel hopefully. 

"Yes Cas. All of you." Dean closes the distance between them and pours all the frustrations and emotions of the past few years into the kiss. It's violent but tender, passionate and loving. Dean can't explain it but as Cas softens into it and returns it and quickly overpowers it, the kiss becomes something more. More like a claiming. It's the best kiss Dean's ever had. He feels... loved. 

 

~~~~~  
Dean loves his boyfriend Cas. Everyone knows that. In public they hold hands and go on dates and kiss whenever they feel like it. He likes to think that, wherever he is, Sam is proud of him. Dean and Cas are a great couple, always on the road in the Impala together and hunting down monsters and rogue demons. They're inseparable. And after hunts, they get back to the motel and Dean lets Cas take control. Cas demands his total focus and his total submission in the bedroom and most of the time Dean is happy to give it to him. 

Castiel is very possessive of him and sometimes Dean likes to test the boundaries and flirt with a sexy woman or an attractive man. Castiel does not tolerate these transgressions and Dean finds himself with a sore ass for days, which of course encourages him to do it more often. Dean likes to toe the line and live dangerously.

Given their stressful lifestyle, their relationship isn't perfect. Cas thinks Dean too reckless and Dean thinks Cas too controlling. They fight and sometimes Dean sneaks out and sleeps with Crowley to get back at Castiel, but it never lasts. He goes back to Cas and begs for forgiveness. Cas always takes him back but doesn't forgive him right away. 

He makes Dean sleep in a different bed until Dean can't stand it anymore. Cas will get out an impressive collection of restraints and toys. There are even clamps and feathers. When Dean's been particularly bad, Cas trusses him up and leaves him at the mercy of a brutal fucking machine, coldly mechanical and unresponsive to Dean's pleading. 

On other days, Cas will do the teasing himself. He takes his time opening up Dean, ignoring his pleading. He's older than civilization. He has nothing but time now. Dean is mortal and only human. He doesn't have an eternity of patience to temper him. They go at Cas's pace and Cas relishes taking Dean apart piece by piece. 

However he starts Dean's punishment, it always ends with Castiel buried deep in Dean, pounding away until he's sure that Dean won't be walking the next day so he can take advantage of his immobility and remind him that the angel should be shown respect. Once Dean remembers, Cas reminds him that he deserves to be loved. 

It isn't perfect but nothing in Dean Winchester's life has ever been. Even still, he wouldn't trade it for anything. He loves it all.


End file.
